Venus Williams and 10 Other Historic Wimbledon Upsets

Tennis’s top venue said an early goodbye to one of its most familiar faces on Monday when Venus Williams lost in consecutive sets in the first round at Wimbledon. Williams has five Wimbledon titles under her belt, but that wasn’t enough to intimidate her opponent Elena Vesnina who cruised 6-1, 6-3 against one of the sport’s best. How does Vesnina’s upset stack up against other impressive wins in the tournament’s illustrious history? Here’s a look back at 10 of the best Wimbledon upsets.

PETE SAMPRAS – 2002

Maybe it was a sign to the tennis legend that it was time to hang up his racket once and for all as Pete Sampras exited in the second round, losing to the 145th-ranked George Bastl. Although he didn’t retire until August 2003, it was this Wimbledon loss that showed things coming apart for him. Bastl took it 6-3, 6-2, 4-6, 3-6, 6-4 after Sampras put together a ferocious rally to send the match deep into a 5th set. Ultimately, though, he couldn’t make up enough ground.

ROGER FEDERER – 2011

At last year’s event, it was Jo-Wilfried Tsonga’s turn to knock off a champion. Only this time it was Roger Federer who got out fast, taking the first two sets 6-3, 7-6 (7-3) and seemingly on his way to yet another semifinals. That’s when things radically shifted, as Tsonga rallied back against Federer who appeared to lack the intensity and enthusiasm to keep up with his opponent. Tsonga dominated the last sets to win the match.

STEFFI GRAF – 1994

Steffi Graf most likely didn’t expect to get much of a challenge from unseeded Lori McNeil, but the five-time Wimbledon champion got more than she bargained for. She suffered a 7-5, 7-6 (7-5) defeat, the first time in the tournament’s history that a defending women’s champion was beaten in the first round. IHow good had Graf been leading up to that match? It was only the second time in a decade that Graf dropped consecutive matches. “She played better than me,” Graf said after the match. “That’s very obvious.”

JOHN MCENROE – 1985

Kevin Curren kept McEnroe, a man who played in the previous five Wimbledon finals, to just eight games in a 6-2, 6-2, 6-4 trouncing in the quarterfinals. “The only time I can remember when I felt so overwhelmed on a tennis court was against (Ivan) Lendl in Dallas, in about 1982,” McEnroe said afterwards. McEnroe was critical of the way he played, saying he was never really in the match, mentally. It’s not as if Curren was a total unknown at the time, though — he was seeded No. 8. But the kind of dismantling he delivered was unprecedented. Curren had only taken one set from McEnroe in their previous seven meetings.

MARTINA HINGIS – 1999

Martina Hingis lost 6-2, 6-0 in the opening round to Jelena Dokic, all of 16 years of age and ranked 129th at the time. Dokic had been a top-ranked junior the previous year so it wasn’t totally out of left field, but Hingis was the world number one entering the match and nobody thought Dokic had a chance to make a name for herself so soon. She swept the final 11 games of the match and required just 54 minutes to oust the popular Hingis. It was the beginning of the end of an era of her rule.

ANDRE AGASSI – 1996

Doug Flach figured out what the rest of the tennis world couldn’t — how to beat Andre Agassi. He took out the No. 3 seed 2-6, 7-6 (7-1), 6-4, 7-6 (8-6) in the first round of the tournament. Agassi was actually one of four seeds to lose the opening day, joining No. 6 Michael Chang, No. 8 Jim Courier and No. 15 Arnaud Boetsch at the exits. The previous time Agassi was sent home in the first round at Wimbledon was in 1987, his first time competing there. For Agassi, it came after a disappointing second-round ouster at the French Open, too.

MARTINA NAVRATILOVA – 1991

It was at once a farewell to one tennis great and a hello to a new one. Jennifer Capriati, at age 15, took out defending champion Martina Navratilova on tennis’ biggest stage. It happened in a women’s quarterfinal, leaving the 34-year-old veteran to deal with a 6-4, 7-5 stunner. Navratilova won at Wimbledon nine times prior. Capriati didn’t come out of nowhere — she was seeded No. 9 the year before, but winning against such a legend at Wimbledon is a Capriati achievement nobody soon forgot.

jimmy CONNORS – 1975

When Jimmy Connors went down, he was on the losing end of a match that would make history. Arthur Ashe in turn became the first black man to win at Wimbledon (Althea Gibson won in 1958 on the women’s side). Ashe put together a career full of firsts, dating back to his time as the National Junior Indoor tennis title and the first black player to be selected to the United States Davis Cup team. Entering the match, Ashe was a heavy underdog, but he took the match 6-1, 6-1, 5-7, 6-4.

lleyton HEWITT – 2003

Defending champion Lleyton Hewitt faced a daunting opponent in the 6-foot-10 Ivo Karlovic, but nobody would have predicted that Karlovic would roll to a 1-6, 7-6 (5), 6-3, 6-4 victory. Karlovic’s world rank at the time? 203. Karlovic swatted back everything that Hewitt sent at him: “This was a case of Goliath getting the better of David,” Sports Illustrated said about the match.

goran IVANISEVIC’S COMPETITION – 2001

This wasn’t just one match; this was a historic run all the way through to capture an improbably championship. Goran Ivanisevic had fallen to No. 125 and earned a wildcard to get into Wimbledon. But he put together win after win against top players like Carlos Moya, Andy Roddick and Marat Safin to get all the way to a semifinal match against Tim Henman. After taking care of Henman, he defeated Patrick Rafter 6–3, 3–6, 6–3, 2–6, 9–7 to take home the title. Ivanisevic became the lowest-ranked player and the first wildcard entry to win Wimbledon. Quite a run indeed.